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Chelate with functions of protecting nerve cells

A compound and selected technology can be used in the preparation of organic compounds, nervous system diseases, medical preparations containing active ingredients, etc., which can solve the problems of complex brain injury mechanism and affecting the prognosis of stroke.

Inactive Publication Date: 2013-10-30
CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This is mainly because the mechanism of brain injury after ischemic stroke is relatively complex. An ideal neuroprotective drug should protect the entire neurovascular unit, protect ischemic brain tissue, and reduce brain damage. Neuroprotection emphasizes "Early" and "protective" should generally be used within 3 to 6 hours (neuroprotective time window), but all neuroprotective agents are currently in the experimental stage, and no independent neuroprotective agent has been shown to affect the prognosis of stroke , there is no preparation on the market at home and abroad

Method used

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  • Chelate with functions of protecting nerve cells
  • Chelate with functions of protecting nerve cells
  • Chelate with functions of protecting nerve cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The preparation of embodiment 1 compound 1

[0036]

[0037] first step

[0038] Using a known method, dissolve o-nitrophenol (45g, 323.5mmol) in N, N'-dimethylformamide (500ml), add 1,2-dibromoethane (30.4g, 161.7mmol), Sodium hydroxide (19.4g, 485.3mmol), reflux reaction for 24h, TLC traced the reaction to be complete, filtered while hot, poured the filtrate into water (2000ml) while stirring, stood at room temperature for 2h, filtered, washed the filter cake with water, and dried 1-a (49.2 g, pale yellow solid) was obtained, yield: 50%.

[0039] MS m / z(ESI): 305.3[M+1]

[0040] 1 H-NMR (400 MHz, Chloroform) δ 8.29-8.21 (m, 1H), 7.81-7.68 (m, 2H), 6.88-6.80 (m, 1H), 4.50 (s, 2H).

[0041] second step

[0042] Using a known method, dissolve 1-a (40g, 131.5mmol) in ethanol (200ml), add 10% wet base palladium carbon (10g), feed hydrogen, react at room temperature overnight, follow the reaction by thin layer chromatography, filter , the filtrate was concentrated ...

Embodiment 2

[0069] The preparation of embodiment 2 compound 2

[0070]

[0071] The first to seven steps are the same as the first to seven steps of embodiment 1;

[0072] eighth step

[0073] Using a known method, dissolve 1-g (700mg, 1.3mmol) in N-methylpyrrolidone (5ml), add n-octyl-monoxyethylene (244mg, 1.4mmol), react overnight at 70°C, and thin layer Chromatography traced the complete reaction, added saturated sodium bicarbonate solution to adjust pH ≈ 8, extracted impurities with dichloromethane, adjusted pH ≈ 3 with 2N hydrochloric acid solution in the aqueous phase, filtered, washed the filter cake with water, and dried to obtain 2 (541.6mg, off-white solid), yield: 57%.

[0074] MS m / z(ESI):731.9[M+1]

[0075] 1 H-NMR (400MHz, Chloroform) δ6.87-6.75(m, 4H), 6.75-6.63(m, 4H), 5.10(s, 1H), 4.69-4.58(m, 3H), 4.49(s, 4H) , 4.38(s, 1H), 4.14(d, 6H), 3.88(s, 1H), 3.61(d, 2H), 3.36-3.26(m, 2H), 1.68-1.38(m, 8H), 1.38-1.14 (m, 14H), 0.98-0.81 (m, 6H).

Embodiment 3

[0076] The preparation of embodiment 3 compound 3

[0077]

[0078] The first to seven steps are the same as the first to seven steps of embodiment 1;

[0079] eighth step

[0080] Using a known method, dissolve 1-g (700mg, 1.3mmol) in N-methylpyrrolidone (5ml), add 2-octadecyloxyethanol (440.4mg, 1.4mmol), react at 70°C overnight, thin The reaction was followed by layer chromatography, adding saturated sodium bicarbonate solution to adjust pH ≈ 8, extracting impurities with dichloromethane, adjusting pH ≈ 3 with 2N hydrochloric acid solution in the aqueous phase, filtering, washing the filter cake with water, and drying to obtain 3 (622.9mg, analogue White solid), yield: 55%.

[0081] MS m / z(ESI): 872.2[M+1]

[0082] 1 H-NMR (400MHz, Chloroform) δ6.89-6.76(m, 4H), 6.76-6.64(m, 4H), 5.04(s, 1H), 4.74(s, 1H), 4.56(s, 1H), 4.50 (d, 5H), 4.28(s, 1H), 4.20(d, 3H), 4.13(t, 2H), 4.04(s, 1H), 3.70(s, 1H), 3.63(t, 2H), 3.33( t, 2H), 1.69-1.18 (m, 44H), 0.97-0.82 (m, 6H).

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Abstract

The invention discloses a chelate and a preparation method. According to impact tests on focal ischemia-reperfusion model rats, the chelate has good functions of protecting nerve cells both in behavioral scoring and cerebral infarction size, and can be used for preparation of neuroprotective agents.

Description

technical field [0001] The present invention relates to a kind of chelate compound and its preparation method and application as neuroprotective drug. Background technique [0002] Stroke, medically known as cerebrovascular accident (CVA), refers to the rapid development of brain function loss due to disorder of blood supply to the brain. It may be caused by ischemia (lack of blood flow) caused by blockage by a blood clot (arterial embolism), or by hemorrhage (leakage of blood). The affected area of ​​the brain loses function, which may cause one or more limbs on one side of the body to be unable to move, understand speech or speak. [0003] Stroke is a medical emergency that will lead to permanent neurological damage, complications and death. It is usually divided into two types: ischemic and hemorrhagic. Stroke is mainly caused by rupture of cerebral blood vessels or structural abnormalities of cerebral blood vessels. Acute ischemic stroke is the most common type of str...

Claims

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Application Information

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IPC IPC(8): C07D213/74C07C229/38C07C227/12A61K31/223A61K31/444A61P9/10A61P25/00
Inventor 王颖向永哲岑国栋
Owner CHENGDU EASTON BIOPHARMACEUTICALS CO LTD
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